To say Maui packs a lot into a little more than 727 square miles is an understatement of irresponsible proportions. Because of its unique geography and infamous trade winds, Maui has multiple distinct microclimates to play in, which help define Maui’s diverse regions. The North Shore and West and Central Maui get a lot of love from tourists, but South Maui and the Upcountry stole our hearts.
For the best view of the island, consider taking a road trip through Maui. We’ve compiled the best pitstops and excursions so you can sit back and enjoy the ride.
Roadtrip One: Upcountry on Kula Highway
On the slopes of Haleakala, tour farms and ranches and peruse local art galleries and markets steeped in the history of Maui’s Paniolo (cowboy) culture. There will be plenty of fresh snacks along the way, finished with a flight of local wine.
1. Paia Town
This historic town on Maui’s North Shore was once a booming plantation town during the height of Maui’s sugar cane industry. Today, Paia is a town of colorful storefronts, local art galleries and one-of-a-kind boutiques and restaurants. On your way out of town, tour the Haliimaile Pineapple Farm and distillery and grab some Maui Gold pineapple to take home.
2. Makawao Town
Makawao is a thriving arts community that has kept its plantation roots intact. The combination of its paniolo heritage and its lively art scene makes for great pop-up markets to eclectic art galleries. The Hui Noeau Visual Arts Center hosts free exhibits and T. Komoda Store & Bakery has been serving cream puffs since 1916.
Boasting spectacular views of two Maui coastlines, Pukalani has a laid-back, country feel. It is home to the Upcountry Farmers Market, which has a wide selection of local growers and producers. Visit one of Maui’s last true mom-and-pop establishments, the Pukalani Superette.
Kula is in the heart of Maui’s Upcountry and in the middle of a culinary resurgence. Harvest your own veggies and have them made into a gourmet meal at Oo Farm, visit the one-man working protea and coffee farm, Shim Coffee Farm, play with the animals at Surfing Goat Dairy or tour the Kula Botanical Gardens.
Blink and you’ll miss the small town of Keokea, but the old-time gas station, art gallery and country general store are worth a visit. Then continue down the road to the Ulupalakua Ranch Store & Grill (famous for their elk) and, finally, reward yourself with a flight of your new favorite wine at Maui Wine.
Roadtrip Two: Hana Highway
Hike to waterfalls and through rain forests, sun on stunning black or red sand beaches and eat the best banana bread you’ve ever had. Do it on your own or hire a guide (or the middle option of downloading a guided tour app like GPSY). Spread it over two days or start early and try to do it all in one. Even though it’s only 50 miles or so, the one-lane bridges, tight turns and incredible views will slow you down. Be sure to stay on the main drag out of respect for the locals who don’t want to be a tourist attraction.
You’re going to want coffee for this road trip, so start off with a cup of joe in Haiku at Jaws Country Store. From there, it’s not far to the Garden of Eden Arboretum or the Leilani Farm Sanctuary in Haiku to see the local flora and fauna up close.
2. Keanae Peninsula
While technically a slight detour from the famous Road to Hana, the ocean views from the Keanae Lookout will change your life, as will a loaf (or two) of fresh banana bread from Aunty Sandy’s Famous Banana Bread. In 1946, the entire community was almost wiped out by a hurricane and the only building left standing was the local church, which you can still see today.
3. Nahiku Marketplace
Another great place to stretch your legs (and take a potty break) is the Nahiku Marketplace—where you’ll find some outdoor dining. There’s coffee, smoothies and more tasty banana bread at the Nahiku Cafe and an open-air BBQ. Find locally made gifts at the Nahiku Gallery. Between the marketplace and Hana, you’ll find Coconut Glen’s, which people swear by, if you’re game for vegan coconut ice cream.
Get a parking reservation in advance to swim and sunbathe on the beautiful black sand beach at Waianapanapa State Park. Or take a (slightly scary) little hike to find the more secluded red sand beach, Kaihalulu Beach. Explore the Hana Lava Tube or Wailua Falls and swimming hole. For souvenirs to commemorate the drive, try the Hasegawa General Store and Hana Ranch Store.
5. Kipahulu District (Haleakala National Park)
A final stretch of stunning rainforest and waterfalls will take you to the Kipahulu District entrance of Haleakala National Park and access the Pipiwai and Kuloa Point trails. The Kuloa Point Trail will take you on a short walk to the Hale Halawai, a reconstruction of a traditional Hawaiian meetinghouse, archeological sites and the Ohe’o Gulch. The Pools of ‘Ohe’o are a stunning series of tiered pools fed by a waterfall, sometimes called the “Seven Sacred Pools.”
Go Big on The Big Island
The Big Island truly lives up to its name (which is actually Hawai’i, while the entire state’s name is Hawaii, which feels like a practical joke to confuse Haoles). Anyway, it’s big. So it’s best to divide your time between its two distinct sides: Hilo Side (wet) and Kona Side (dry).
Hilo Bay, at the center of Hilo Town, is a good place to start your exploration of the main “city” on the wet side. From the Bay, it’s an easy walk to Liliuokalani Gardens and a stroll through Hilo’s Farmer Market to pick up picnic supplies. Richardson’s Beach Park offers a gentle put-in for snorkeling. From Hilo, drive to Volcanoes National Park for a chance to see the constant volcanic activity bubbling below the surface.
Visit Pu’uhonua o Honaunau National Historical Park (The Place of Refuge) a fascinating dose of early Hawaiian history established on the site of a sanctuary and sacred place of peace.
Nearby is the snorkeling hot spot Kealakekua Bay and the Captain Cook Monument. You can access the monument by kayak or book a charter with Captain Zodiac Raft Tours and enjoy snorkeling in the bay near the monument. The eastern side of the island is home to its best sandy beaches. The most popular sandy beach on the east side is Hapuna Beach, be sure to plan for some sand and surf time here. One of the most unique ocean experiences in Hawaii is the opportunity to dive or snorkel with the pod of Manta Rays that live off the coast. Book a charter at the Kona Marina (book early, they are insanely popular). Kona Village is the main city on the Kona side. Explore shops, restaurants and bars on its main street. The Royal Hawaiian Hotel has a beautiful ocean-view bar and an excellent happy hour.